QSAR and pharmacophore analysis on amides against drug-resistant S. aureus

YILDIZ İ., Ertan T., BOLELLİ K., ARPACI Ö., Yalcin I., Aki E.

SAR AND QSAR IN ENVIRONMENTAL RESEARCH, cilt.19, sa.1-2, ss.101-113, 2008 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 19 Sayı: 1-2
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1080/10629360701844159
  • Dergi Adı: SAR AND QSAR IN ENVIRONMENTAL RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.101-113
  • Anahtar Kelimeler: benzamide, phenylacetamide, drug-resistant Staphylococcus aureus, QSAR, 3D-common-feature pharmacophore hypotheses, hiphop, MICROBIOLOGICAL ACTIVITY, POSSIBLE METABOLITES, CONFORMATIONAL COVERAGE, PHENYLACETAMIDES, IDENTIFICATION, VALIDATION
  • Ankara Üniversitesi Adresli: Evet

Özet

Considering the worth of developing new antibacterial agents against drug-resistant Stapylococcus aureus, the present study explores the structure-activity relationships analysis of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives using classical QSAR and 3D-common-feature pharmacophore hypothese approaches. QSAR analysis revealed that the compounds possessing a methylene group between the phenyl and the carboxyamido moiety played a role for decreasing the activity. On the other side, substituent effects on position R-1 was found important for the activity and holding a substituent possessing a minimum width property on this position like as alkyl groups enhanced the activity. Moreover, substituting position R-3 with a group enhancing the electron-donor capability of the phenolic ring system increased the potency. 3D-common-feature pharmacophore approach considered that the conformational properties of the compounds were important for the activity against drug-resistant S. aureus and compounds possessing a benzamide moiety rather than phenylacetamide structure increased the activity. Furthermore, holding NO2 and OH groups on the phenyl ring attached to the benzamide moiety was important for improving the potency against drug-resistant S. aureus.